DOCSLIB.ORG

A Computational Approach on the Activity of Hesperidin As Antagonist for Proteins of SARS-Cov-2

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
A Computational Approach on the Activity of Hesperidin As Antagonist for Proteins of SARS-Cov-2 Article Volume 10, Issue 3, 2021, 2571 - 2577 https://doi.org/10.33263/LIANBS103.25712577 A Computational Approach on the Activity of Hesperidin as Antagonist for Proteins of SARS-CoV-2 Satyanarayana Swamy Vyshnava 1 , Dileep Kumar Kanderi 2 , Shiva Prasad Panjala 3, Kameshpandian Paramasivam 4 , Gayathri Pandluru 1, Swathi Banapuram 3, Roja Rani Anupalli 3, Muralidhara Rao Dowlatabad 1, * 1 Department of Biotechnology, Sri Krishnadevaraya University, Anantapuram, A.P, India 2 Department of Microbiology, Sri Krishnadevaraya University, Anantapuram, A.P, India 3 Department of Genetics and Biotechnology, Osmania University, Hyderabad, T.S, India 4 Department of Forensic science, Ultra arts, and science college, Madurai, T.N, India * Correspondence: [email protected]; Scopus Author ID 36446251900 Received: 21.12.2020; Revised: 10.01.2021; Accepted: 12.01.2021; Published: 20.01.2021 Abstract: Spike proteins are a functional component in the viral infections of the SARS-CoV-2 virus that binds to the ACE2 receptors of the human cells. The naturally derived drugs like hesperidin show a higher affinity to avoiding the binding of the spike protein. Inhibition of the spike protein study represents the development of a new drug for SARS disease. Along with the hesperidin and its analogs have been found effective medicine to control SARS-CoV-2; the entire drug bank database was screened for strong analogous remedy like compounds as hesperidin. Virtual Screening and docking studies were intended for these molecules against spike protein with auto dock virtual screening tool and auto dock vena. The docking outcome showed that the compounds hesperitin, silibilin, and dihydromyricetin were having the highest binding energies, like -8 and -6.2. The current study indicates that the lead molecules have to be evaluated to improve prospective drug molecules. Keywords: computational drug docking; hesperidin; spike protein; SARS-CoV-2. © 2020 by the authors. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). 1. Introduction A health emergency and rapid infection transmission rate were created by the amid an outbreak of global pandemic COVID-19. There is a spent argument on the origin of the virus, where it comes from and affecting almost all countries levels of spread and severity of the certain alarming levels as mention by WHO, characterized as a pandemic. The novel corona is creating a panic situation worldwide due to inadequate risk assessment, research, and treatment regarding the pandemic's urgency. Due to increased globalization, intra-regional and country travels to make the global epidemics threaten public health, with a very little preventive measure and antiviral therapies revealing viral infections remained only with few antiviral drugs adopted for medical practice. Naturally occurring large groups of biochemicals such as terpenoids, flavonoids, phenolic compounds, etc., from the plant sources, may look at potential drug molecules to treat the deadly diseases [1]. One such compound hesperidin, which is a glycosidic phenolic flavonoid compound and it is abundant in citric fruits such as lemons, grapefruits, etc., This flavonoid shows anti-inflammatory, anti-fungal, antibacterial, antiviral, antioxidant, and free radical scavengers against many pathogenic and immunomodulatory activities [2-4]. The https://nanobioletters.com/ 2571 https://doi.org/10.33263/LIANBS103.25712577 molecular studies and docking studies refer to the potential application of hesperidin in treating microbial infections [4], neurological disorders like Parkinson and Alzheimer's disease [5,6], anti-inflammatory activity [7], anti-cancer activity [8], and other in-silico studies of the modified to nanoparticles in the application of antioxidant activity [9]. In-silico studies in identifying the antiviral drugs against COVID-19 are processed in recent literature, where hesperidin is one of its kind shows the potential application in inhibiting the protease [10-12] and other related proteins of the Coronavirus 2 [13]. After considering the potential application of hesperidin, in this study, we have found the antiviral activity of hesperidin and its derivatives as listed in the drug bank using the in-silico analysis. 2. Materials and Methods 2.1. Protein preparation. The target protein crystal structure, the spike core protein, was acquired from the protein data bank with pdb id1WNC along with other target proteins include1QZ8, 6W4Band 3EE7 (which are Nsp9 RNA binding proteins structures), and 6W63 (main protease) [14]. Using the discovery studio client, the targeted proteins' molecular coordinates were estranged, and its geometry was optimized for the ligand interactions during the docking workplace in .pdbqt format [15]. 2.2. Binding site prediction. Finding molecular coordinates is the most critical step in molecular docking in the modern era of drug design. A large number of online algorithms are available to find the active sites for the selected target proteins; in this study, to find the active site for the respective receptors, we acknowledged using the online platform playmolecule_Deep Site server [16]. This program, playmolecule_Deep Site, is used to locate and measure protein pockets and cavities mechanically and is based on accurate computational geometry methods and alpha form, and distinct flow theory. 2.3. Ligand preparation. In this study, plant-based flavanone glycoside hesperidin, abundant in citrus fruits, was used to study the activity against the SARS-COV-2. We acquired the requisite files (.sdf and .pdb) from the drug bank with ID DB04703 for hesperidin. With hesperidin compound, its potential analogs were used in an assay for the binding on the viral in targeted proteins [17]. Using auto dock tools 4.0, the ligands are optimized for docking by creating the atomic coordinates with .pdbqt formats [18]. 2.4. Virtual screening. In this study, the most powerful yet reliable platform, Auto dock 4.0, was implemented for the virtual screening of the hesperidin and its analogs to the targeted proteins of COVID- 19. Based on the standard operations' Auto dock execution, provide a list of outcomes to be ordered in the rank based on the affinity-based grading system. https://nanobioletters.com/ 2572 https://doi.org/10.33263/LIANBS103.25712577 2.5. Structural analysis and visualization. The powerful tools represent analysis and illustration of the protein-ligand interactions include PyMol from Schrödinger [19] and Discovery studio client from the Dassault Systèmes [15]. 3. Results and Discussion Playmolecule_Deep Site server provides the possible coordinates for the active site for the respective protein molecules, where 1WNC has core three active sites with active amino acids include THR 921, GLY 928, ASP932, GLN 931, LYS 946, GLN 1161, ASN 1168 involves in considerably in binding and catalytic activity. The Virtual screening of the ligands in Fig 1 includes hesperidin and its structural analogs Hesperetin, Taxifolin, Sakuranetin, Silibinin and Dihydromyricetin were capable approach in potential inhibitors in the ACE 2 (Angiotensin 2 Receptor) binding in the SARS COV2 virus based on the values obtained in the order -8, -5.7, -6.1, -5.3and -6.2 Kcal/Mol. When comparing the other protein structure include Nsp9 RNA binding proteins structures of positive-strand of SARS COV2 virus with PDB IDs 1QZ8, 6W4B and 3EE7, 3EE7 had better binding affinities than the other Nsp9 binding protein. This may occur due to the available active site amino acids' potential to form the higher affinity binding in the 3EE7 rather than that of other Nsp9 Proteins based on this docking study. The binding of the ligand on the targeted Nsp9 protein suggests that hesperidin and its analogs have a considerable function in the self-assembly of the proteins during the replication of the virus for the RNA binding, which may provide an effective drug model for the treatment of COVID-19 patients to stop the intracellular transmission of the viruses. https://nanobioletters.com/ 2573 https://doi.org/10.33263/LIANBS103.25712577 Figure 1. Molecular docking of the 1WNC, the spike protein core structure, had profound activity in the binding on the angiotensin receptor 2 (ACE 2). (a) Hesperetin with -8.0 Kcal/Mol, (b) Taxifolin with -5.7 Kcal/Mol, (c) Sakuranetin with -6.1 Kcal/Mol, (d) Silibininwith -5.3 Kcal/Mol, and (e) Dihydromyricetin with -6.2 Kcal/Mol affinities for arbitrary activities include inhibition and inactivation of the protein. https://nanobioletters.com/ 2574 https://doi.org/10.33263/LIANBS103.25712577 Protease, also called the main protease, is the potential source of infections of SARS- COV-2 viruses. The inhibitory activity was well studied and understood from the recent investigations by in-silico analysis states the enzyme inactivation and blocking the cellular receptor for the protease activity [12]. Based on this source, our targeted main protease protein with PDB ID 6W63 had reproduced similar results with hesperidin analogs with values ranges from -5.4 for hesperetin, -5.6 for dihydromyricetin, and -5.8 for taxifolin. The virtual screening results for the targeted protein with respective ligands for the presented study are listed and compared in Fig 2 (detailed discussion is elaborated in Table 1), where for the overall study, the highest binding affinity was higher with -8.0 Kcal/Mol in the 1WNC with hesperidin molecule. 1WNC spike core protein variance in the amino acid residual functions are studied using the molecular simulations with references to the RMSF with minimal changes in the residual fluctuations, which refers to the binding affinity for respective ligands are shown in Fig 3. This shows the functional activity of 1WNC during its bindings to the respective ligands include hesperidin and its structural analogs. Among the docked ligands of hesperidin and its analogs on the Nsp9 protein, main protease and Spike core protein had a very higher tendency, which may have arbitrary effects include inhibition of the protein to bind the ACE 2 receptor on the COVID-19 patients to block the infections of the SARS COV2 virus.
Load more

Recommended publications
  • Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: a Review
    molecules Review Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: A Review Hanghang Lou 1,†, Lifei Hu 2,†, Hongyun Lu 1, Tianyu Wei 1 and Qihe Chen 1,* 1 Department of Food Science and Nutrition, Zhejiang University, Hangzhou 310058, China; [email protected] (H.L.); [email protected] (H.L.); [email protected] (T.W.) 2 Hubei Key Lab of Quality and Safety of Traditional Chinese Medicine & Health Food, Huangshi 435100, China; [email protected] * Correspondence: [email protected]; Tel.: +86-0571-8698-4316 † These authors are equally to this manuscript. Abstract: Flavonoids belong to a class of plant secondary metabolites that have a polyphenol structure. Flavonoids show extensive biological activity, such as antioxidative, anti-inflammatory, anti-mutagenic, anti-cancer, and antibacterial properties, so they are widely used in the food, phar- maceutical, and nutraceutical industries. However, traditional sources of flavonoids are no longer sufficient to meet current demands. In recent years, with the clarification of the biosynthetic pathway of flavonoids and the development of synthetic biology, it has become possible to use synthetic metabolic engineering methods with microorganisms as hosts to produce flavonoids. This article mainly reviews the biosynthetic pathways of flavonoids and the development of microbial expression systems for the production of flavonoids in order to provide a useful reference for further research on synthetic metabolic engineering of flavonoids. Meanwhile, the application of co-culture systems in the biosynthesis of flavonoids is emphasized in this review. Citation: Lou, H.; Hu, L.; Lu, H.; Wei, Keywords: flavonoids; metabolic engineering; co-culture system; biosynthesis; microbial cell factories T.; Chen, Q.
    [Show full text]
  • Chromanone-A Prerogative Therapeutic Scaffold: an Overview
    Arabian Journal for Science and Engineering https://doi.org/10.1007/s13369-021-05858-3 REVIEW-CHEMISTRY Chromanone‑A Prerogative Therapeutic Scafold: An Overview Sonia Kamboj1,2 · Randhir Singh1 Received: 28 September 2020 / Accepted: 9 June 2021 © King Fahd University of Petroleum & Minerals 2021 Abstract Chromanone or Chroman-4-one is the most important and interesting heterobicyclic compound and acts as a building block in medicinal chemistry for isolation, designing and synthesis of novel lead compounds. Structurally, absence of a double bond in chromanone between C-2 and C-3 shows a minor diference from chromone but exhibits signifcant variations in biological activities. In the present review, various studies published on synthesis, pharmacological evaluation on chroman- 4-one analogues are addressed to signify the importance of chromanone as a versatile scafold exhibiting a wide range of pharmacological activities. But, due to poor yield in the case of chemical synthesis and expensive isolation procedure from natural compounds, more studies are required to provide the most efective and cost-efective methods to synthesize novel chromanone analogs to give leads to chemistry community. Considering the versatility of chromanone, this review is designed to impart comprehensive, critical and authoritative information about chromanone template in drug designing and development. Keywords Chroman-4-one · Chromone · Pharmacological activity · Synthesis · Analogues 1 Introduction dihydropyran (ring B) which relates to chromane, chromene, chromone and chromenone, but the absence of C2-C3 dou- Chroman-4-one is one of the most important heterobicyclic ble bond of chroman-4-one skeleton makes a minor difer- moieties existing in natural compounds as polyphenols and ence (Table 1) from chromone and associated with diverse as synthetic compounds like Taxifolin, also known as chro- biological activities [1].
    [Show full text]
  • Chondroprotective Agents
    Europaisches Patentamt J European Patent Office © Publication number: 0 633 022 A2 Office europeen des brevets EUROPEAN PATENT APPLICATION © Application number: 94109872.5 © Int. CI.6: A61K 31/365, A61 K 31/70 @ Date of filing: 27.06.94 © Priority: 09.07.93 JP 194182/93 Saitama 350-02 (JP) Inventor: Niimura, Koichi @ Date of publication of application: Rune Warabi 1-718, 11.01.95 Bulletin 95/02 1-17-30, Chuo Warabi-shi, 0 Designated Contracting States: Saitama 335 (JP) CH DE FR GB IT LI SE Inventor: Umekawa, Kiyonori 5-4-309, Mihama © Applicant: KUREHA CHEMICAL INDUSTRY CO., Urayasu-shi, LTD. Chiba 279 (JP) 9-11, Horidome-cho, 1-chome Nihonbashi Chuo-ku © Representative: Minderop, Ralph H. Dr. rer.nat. Tokyo 103 (JP) et al Cohausz & Florack @ Inventor: Watanabe, Koju Patentanwalte 2-5-7, Tsurumai Bergiusstrasse 2 b Sakado-shi, D-30655 Hannover (DE) © Chondroprotective agents. © A chondroprotective agent comprising a flavonoid compound of the general formula (I): (I) CM < CM CM wherein R1 to R9 are, independently, a hydrogen atom, hydroxyl group, or methoxyl group and X is a single bond or a double bond, or a stereoisomer thereof, or a naturally occurring glycoside thereof is disclosed. The 00 00 above compound strongly inhibits proteoglycan depletion from the chondrocyte matrix and exhibits a function to (Q protect cartilage, and thus, is extremely effective for the treatment of arthropathy. Rank Xerox (UK) Business Services (3. 10/3.09/3.3.4) EP 0 633 022 A2 BACKGROUND OF THE INVENTION 1 . Field of the Invention 5 The present invention relates to an agent for protecting cartilage, i.e., a chondroprotective agent, more particularly, a chondroprotective agent containing a flavonoid compound or a stereoisomer thereof, or a naturally occurring glycoside thereof.
    [Show full text]
  • Evaluation of Anticancer Activities of Phenolic Compounds In
    EVALUATION OF ANTICANCER ACTIVITIES OF PHENOLIC COMPOUNDS IN BLUEBERRIES AND MUSCADINE GRAPES by WEIGUANG YI (Under the Direction of CASIMIR C. AKOH) ABSTRACT Research has shown that diets rich in phenolic compounds may be associated with lower risk of several chronic diseases including cancer. This study systematically evaluated the bioactivities of phenolic compounds in blueberries and muscadine grapes, and assessed their potential cell growth inhibition and apoptosis induction effects using two colon cancer cell lines (HT-29 and Caco-2), and one liver cancer cell line (HepG2). In addition, the absorption of blueberry anthocyanin extracts was evaluated using Caco-2 human intestinal cell monolayers. Polyphenols in three blueberry cultivars (Briteblue, Tifblue and Powderblue), and four cultivars of muscadine (Carlos, Ison, Noble, and Supreme) were extracted and freeze dried. The extracts were further separated into phenolic acids, tannins, flavonols, and anthocyanins using a HLB cartridge and LH20 column. In both blueberries and muscadine grapes, some individual phenolic acids and flavonoids were identified by HPLC with more than 90% purity in anthocyanin fractions. The dried extracts and fractions were added to the cell culture medium to test for cell growth inhibition and induction of apoptosis. Polyphenols from both blueberries and muscadine grapes had significant inhibitory effects on cancer cell growth. The phenolic acid fraction showed relatively lower bioactivities with 50% inhibition at 0.5-3 µg/mL. The intermediate bioactivities were observed in the flavonol and tannin fractions. The greatest inhibitory effect among all four fractions was from the anthocyanin fractions in the three cell lines. Cell growth was significantly inhibited more than 50% by the anthocyanin fractions at concentrations of 15-300 µg/mL.
    [Show full text]
  • Interactions with Microbial Proteins Driving the Antibacterial Activity of Flavonoids
    pharmaceutics Review Interactions with Microbial Proteins Driving the Antibacterial Activity of Flavonoids Giuliana Donadio 1,†, Francesca Mensitieri 2,†, Valentina Santoro 1, Valentina Parisi 1,3, Maria Laura Bellone 1,3, Nunziatina De Tommasi 1, Viviana Izzo 2 and Fabrizio Dal Piaz 2,* 1 Department of Pharmacy, University of Salerno, 84084 Fisciano, Italy; [email protected] (G.D.); [email protected] (V.S.); [email protected] (V.P.); [email protected] (M.L.B.); [email protected] (N.D.T.) 2 Department of Medicine and Surgery, University of Salerno, 84082 Baronissi, Italy; [email protected] (F.M.); [email protected] (V.I.) 3 PhD Program in Drug Discovery and Development, Department of Pharmacy, University of Salerno, 84084 Fisciano, Italy * Correspondence: [email protected] † These authors contributed equally to this work. Abstract: Flavonoids are among the most abundant natural bioactive compounds produced by plants. Many different activities have been reported for these secondary metabolites against numerous cells and systems. One of the most interesting is certainly the antimicrobial, which is stimulated through various molecular mechanisms. In fact, flavonoids are effective both in directly damaging the envelope of Gram-negative and Gram-positive bacteria but also by acting toward specific molecular targets essential for the survival of these microorganisms. The purpose of this paper is to present an overview of the most interesting results obtained in the research focused on the study of the Citation: Donadio, G.; Mensitieri, F.; interactions between flavonoids and bacterial proteins. Despite the great structural heterogeneity Santoro, V.; Parisi, V.; Bellone, M.L.; of these plant metabolites, it is interesting to observe that many flavonoids affect the same cellular De Tommasi, N.; Izzo, V.; Dal Piaz, F.
    [Show full text]
  • Biochemical Characterization of a Flavonoid O-Methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production
    molecules Article Biochemical Characterization of a Flavonoid O-methyltransferase from Perilla Leaves and Its Application in 7-Methoxyflavonoid Production 1, 2, 1 1 1 Hye Lin Park y, Jae Chul Lee y, Kyungha Lee , Jeong Min Lee , Hyo Jeong Nam , Seong Hee Bhoo 1,3, Tae Hoon Lee 2,3, Sang-Won Lee 1,* and Man-Ho Cho 1,3,* 1 Department of Genetic Engineering, Kyung Hee University, Yongin 17104, Korea; [email protected] (H.L.P.); [email protected] (K.L.); [email protected] (J.M.L.); [email protected] (H.J.N.); [email protected] (S.H.B.) 2 Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea; [email protected] (J.C.L.); [email protected] (T.H.L.) 3 Global Center for Pharmaceutical Ingredient Materials, Kyung Hee University, Yongin 17104, Korea * Correspondence: [email protected] (S.-W.L.); [email protected] (M.-H.C.) These authors equally contributed to this work. y Academic Editors: Sławomir Dresler and Barbara Hawrylak-Nowak Received: 3 September 2020; Accepted: 25 September 2020; Published: 28 September 2020 Abstract: Methylation is a common structural modification that can alter and improve the biological activities of natural compounds. O-Methyltransferases (OMTs) catalyze the methylation of a wide array of secondary metabolites, including flavonoids, and are potentially useful tools for the biotechnological production of valuable natural products. An OMT gene (PfOMT3) was isolated from perilla leaves as a putative flavonoid OMT (FOMT). Phylogenetic analysis and sequence comparisons showed that PfOMT3 is a class II OMT.
    [Show full text]
  • Characterization of a Flavonoid 3'/5'/7-O-Methyltransferase
    molecules Article Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the In Vitro Cytotoxicity of Its Methylated Products 1,2,3, 1,2,3, 1,2,3 1,2,3 1,2,3 Xiaojuan Liu y, Yue Wang y , Yezhi Chen , Shuting Xu , Qin Gong , Chenning Zhao 1,2,3, Jinping Cao 1,2,3 and Chongde Sun 1,2,3,* 1 College of Agriculture & Biotechnology, Zhejiang University, Zijingang Campus, Hangzhou 310058, China; [email protected] (X.L.); [email protected] (Y.W.); [email protected] (Y.C.); [email protected] (S.X.); [email protected] (Q.G.); [email protected] (C.Z.); [email protected] (J.C.) 2 Zhejiang Provincial Key Laboratory of Horticultural Plant Integrative Biology, Zhejiang University, Zijingang Campus, Hangzhou 310058, China 3 The State Agriculture Ministry Laboratory of Horticultural Plant Growth, Development and Quality Improvement, Zhejiang University, Zijingang Campus, Hangzhou 310058, China * Correspondence: [email protected]; Tel.: +86-0571-8898-2229 These authors contributed equally to this work. y Received: 18 January 2020; Accepted: 12 February 2020; Published: 15 February 2020 Abstract: O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions.
    [Show full text]
  • Review on Plant Antimicrobials: a Mechanistic Viewpoint Bahman Khameneh1, Milad Iranshahy2,3, Vahid Soheili1 and Bibi Sedigheh Fazly Bazzaz3*
    Khameneh et al. Antimicrobial Resistance and Infection Control (2019) 8:118 https://doi.org/10.1186/s13756-019-0559-6 REVIEW Open Access Review on plant antimicrobials: a mechanistic viewpoint Bahman Khameneh1, Milad Iranshahy2,3, Vahid Soheili1 and Bibi Sedigheh Fazly Bazzaz3* Abstract Microbial resistance to classical antibiotics and its rapid progression have raised serious concern in the treatment of infectious diseases. Recently, many studies have been directed towards finding promising solutions to overcome these problems. Phytochemicals have exerted potential antibacterial activities against sensitive and resistant pathogens via different mechanisms of action. In this review, we have summarized the main antibiotic resistance mechanisms of bacteria and also discussed how phytochemicals belonging to different chemical classes could reverse the antibiotic resistance. Next to containing direct antimicrobial activities, some of them have exerted in vitro synergistic effects when being combined with conventional antibiotics. Considering these facts, it could be stated that phytochemicals represent a valuable source of bioactive compounds with potent antimicrobial activities. Keywords: Antibiotic-resistant, Antimicrobial activity, Combination therapy, Mechanism of action, Natural products, Phytochemicals Introduction bacteria [10, 12–14]. However, up to this date, the Today’s, microbial infections, resistance to antibiotic structure-activity relationships and mechanisms of action drugs, have been the biggest challenges, which threaten of natural compounds have largely remained elusive. In the health of societies. Microbial infections are responsible the present review, we have focused on describing the re- for millions of deaths every year worldwide. In 2013, 9.2 lationship between the structure of natural compounds million deaths have been reported because of infections and their possible mechanism of action.
    [Show full text]
  • Download PDF (Inglês)
    http://dx.doi.org/10.21577/0103-5053.20190039 J. Braz. Chem. Soc., Vol. 30, No. 7, 1437-1446, 2019 Article Printed in Brazil - ©2019 Sociedade Brasileira de Química Assessing the Spatial Distribution of Key Flavonoids in Mentha × piperita Leaves: An Application of Desorption Electrospray Ionization Mass Spectrometry Imaging (DESI-MSI) Julia R. L. e Freitas,a Pedro H. Vendramini,b Júlio O. F. Melo, c Marcos N. Eberlinb and Rodinei Augusti *,a aDepartamento de Química, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte-MG, Brazil bLaboratório ThoMSon de Espectrometria de Massas, Instituto de Química, Universidade Estadual de Campinas, 13083-970 Campinas-SP, Brazil cDepartamento de Química, Universidade Federal de São João Del Rei, 35701-970 Sete Lagoas-MG, Brazil Desorption electrospray ionization mass spectrometry imaging (DESI-MSI) was used to assess the spatial distribution of some key flavonoids in peppermint (Mentha × piperita L.) leaves. The chemical images were generated by applying DESI-MSI on the peppermint leaves imprinting while acquiring the spectra in the negative ion mode. The following key flavonoids were detected and grouped within well-known biosynthetic routes in plants: naringenin route [naringenin, sakuranetin, hesperetin, hesperidin, luteolin, and apigenin]; luteolin route [luteolin, chrysoeriol, luteolin-7-O-D-glucuronide, luteolin-7-O-D-glucoside, luteolin-7-O-neohesperidoside]; apigenin route [apigenin, apigenin-7-O-gentiobioside, apigenin-7-O-neohesperidoside, thymusin/pilosin, pebrellin, acacetin/genkwanin, ladanein, xanthomicrol/pedunculin/nevadensin]. Maps of the spatial distribution of these flavonoids throughout the peppermint leaves within each route were then displayed. The results described herein comprise an important (although still underexplored) subject that certainly will experience a remarkable growth in the next years.
    [Show full text]
  • USDA Database for the Flavonoid Content of Selected Foods
    USDA Database for the Flavonoid Content of Selected Foods Release 3.1 Prepared by Seema Bhagwat, David B. Haytowitz, and Joanne M. Holden (ret.) Nutrient Data Laboratory Beltsville Human Nutrition Research Center Agricultural Research Service U.S. Department of Agriculture December 2013 U.S. Department of Agriculture Agricultural Research Service Beltsville Human Nutrition Research Center Nutrient Data Laboratory 10300 Baltimore Avenue Building 005, Room 107, BARC-West Beltsville, Maryland 20705 Tel. 301-504-0630, FAX: 301-504-0632 E-Mail: [email protected] Web site: http://www.ars.usda.gov/nutrientdata Table of Contents Release History ............................................................................................. i Suggested Citation: ...................................................................................... ii Documentation .............................................................................................1 Subclasses of flavonoids and selected compounds .................................2 Methods and Procedures used to generate the database ........................2 Data Evaluation ........................................................................................4 Flavonoid Individual Data Table ...............................................................5 Sources of Data ...........................................................................................6 Format of the Tables ....................................................................................7 Food Description
    [Show full text]
  • Constitution of Naringin
    CONSTITUTION OF NARINGIN The Position of the Sugar Group By S. RANGAS`VAMI, T. R. SESHADRI AND J. VERRARAGHAVIAH (From the Departments of Chemistry and Chemical Technology, Andhra University, TFaltair) Received February 18, 1939 THE crystalline bitter principle, naringin was first isolated in 1866 by de Vry in Java from grape fruit blossoms. Recently it has been produced in large quantities from grape fruit residues. In the course of our work on the chemistry of Indian fruits we have prepared naringin from the peels and rags of the pamparapanas fruit (Citrus paradisi). When anhydrous the substance has the composition C 7 H 32,O 14 and on hydrolysis with acids gives rise to an aglucone called naringenin along with a molecule of glucose and a molecule of rhamnose. Naringenin has the formula C15IT12O5. Though at first it was thought to be a chalkonel it was finally proved to have the constitution of 5 : 7 : 4'-trihydroxyflavanone (I, R = H) by Asahina and Inubuse2 in 1928. This was confirmed subsequently by its synthesis by Shinoda and Sato 3 by condensing phloroglucinol with the ethyl carbonate of p-coumaric acid in the presence of aluminium chloride. An attempt was made by Asahina and Inubuse 4 to locate the position of the sugars in the molecule of naringin. On heating the substance with barium hydroxide for 12 hours in an atmosphere of hydrogen it was found to yield p-hydroxy-benzaldehyde and a glycoside of phloracetophenone. The latter on further hydrolysis with dilute sulphuric acid yielded phloraceto- phenone, glucose and rhamnose. By the action of diazomethane on naringin a syrupy substance was obtained which on hydrolysis gave a monomethyl ether of naringenin known as iso-sakuranetin (II).
    [Show full text]
  • Impact of Flavonoids Against Woolly Apple Aphid, Eriosoma Lanigerum (Hausmann) and Its Sole Parasitoid, Aphelinus Mali (Hald.)
    www.ccsenet.org/jas Journal of Agricultural Science Vol. 4, No. 2; 2012 Impact of Flavonoids against Woolly Apple Aphid, Eriosoma lanigerum (Hausmann) and Its Sole Parasitoid, Aphelinus mali (Hald.) Mazen Ateyyat (Corresponding author) Faculty of Agricultural Technology, Al-Balqa’ Applied University PO box 19117, Al-Salt, Jordan E-mail: [email protected] Saeid Abu-Romman Faculty of Agricultural Technology, Al-Balqa’ Applied University PO box 19117, Al-Salt, Jordan Mohmmad Abu-Darwish Ash-Shoubak University College, Al-Balqa’ Applied University PO box 19117, Al-Salt, Jordan Ihab Ghabeish Al-Salt University College, Al-Balqa’ Applied University PO box 19117, Al-Salt, Jordan Received: June 16, 2011 Accepted: July 12, 2011 Online Published: December 21, 2011 doi:10.5539/jas.v4n2p227 URL: http://dx.doi.org/10.5539/jas.v4n2p227 The research is financed by Scientific Research Fund, Ministry of Higher Education, Jordan. Abstract Cut-shoot bioassay test was used to study the significance of three flavonoids as aphicides against the woolly apple aphid (WAA), Eriosoma lanigerum (Hausmann). The used flavonoids were two flavanols that are quercetin dehydrate and rutin hydrate, but rutin hydrate is a glycoside of quercetin dehydrate. In addition to one flavanone that was naringine. These flavonoids were used at three concentrations; 100 ppm, 1000 ppm and 10,000 ppm. Results showed that the three tested flavonoids were active as aphicides against the target species and that mortality to nymphs was higher than that obtained against apterous adults. Increasing the concentration of the flavonoids resulted in a remarkable increase in nymphs mortality. However, rutin hydrate is more toxic to WAA than quercetin dehydrate and naringin.
    [Show full text]